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Paper | Special issue | Vol 49, No. 1, 1998, pp.143-148
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S7
Novel Heterocycles: A Benzodithiolane S-Oxide and a Benzothiadiazinane S-Oxide

Alan R. Katritzky,* Zhongxing Zhang, Ming Qi, Nusrallah Jubran, and Louis M. Leichter

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.

Abstract

Synthetic methodology has been developed for the synthesis of novel heterocycles from 3,3-diaryl-3H-2,1-benzoxathiole 1-oxides (2). Cyclic sulfinates (2) were converted directly into 3,3-diaryl-1,2-benzodithiolane 1-oxide (3) and 4,4-diaryl-1,2,3-benzothiadiazinane 1-oxide (4) which represent a cyclic thiosulfinate and a cyclic sulfinyl hydrazide, respectively. 3,7-Bis(dimethylamino)-10-(p-dimethylaminobenzene)thiaxanthene 5,5-dioxide (8a) and 3-dimethylamino-10-(p-dimethylaminobenzene)thiaxanthene 5,5-dioxide (8b) were formed from the reaction of hydrazine and compound (2).